Acetonitrile → 5-Bromo-6-methylpyridine-2-carbonitrile

Temperature

80 °C

3-Bromo-6-iodo-2-methylpyridine (1 equiv) and acetonitrile were combined and copper cyanide (0.5 equiv), sodium cyanide (0.8 equiv) were added. The reaction slurry was heated to 80° C. for 24 h. The reaction solution was cooled to room temperature and diluted with ammonium hydroxide (0.5 M aqueous solution). The mixture was stirred 15-30 min, filtered through diatomaceous earth and the filter cake was washed with ethyl acetate. The filtrate and wash were combined and diluted with ethyl acetate. The aqueous and organic phases were separated and the organic layer was washed with ammonium hydroxide (0.5 M aqueous solution) and saturated aqueous sodium chloride, dried, filtered, and concentrated under reduced pressure to provide 5-bromo-6-methylpicolinonitrile as a. MS (ESI) m/z 196.9 [M]+, 198.9 [M+2]+.

1. temperatureThe reaction solution was cooled to room temperature
2. filtrationfiltered through diatomaceous earth
3. washthe filter cake was washed with ethyl acetate
4. washThe filtrate and wash
5. additiondiluted with ethyl acetate
6. customThe aqueous and organic phases were separated
7. washthe organic layer was washed with ammonium hydroxide (0.5 M aqueous solution) and saturated aqueous sodium chloride
8. customdried
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure

ORD record

ord-2220c42f0a3d4fc5bddeeea5cc09cf73

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09359364B2